DE1670503A1 - Pyrazolidindion-derivate - Google Patents
Pyrazolidindion-derivateInfo
- Publication number
- DE1670503A1 DE1670503A1 DE19681670503 DE1670503A DE1670503A1 DE 1670503 A1 DE1670503 A1 DE 1670503A1 DE 19681670503 DE19681670503 DE 19681670503 DE 1670503 A DE1670503 A DE 1670503A DE 1670503 A1 DE1670503 A1 DE 1670503A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- phenoxyacetic
- pyrazolidine
- phenoxy
- anp
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- CYMJPJKHCSDSRG-UHFFFAOYSA-N pyrazolidine-3,4-dione Chemical class O=C1CNNC1=O CYMJPJKHCSDSRG-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 14
- 229960002895 phenylbutazone Drugs 0.000 claims description 10
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- -1 p-chlorophenoxy Chemical group 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 4
- AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 2
- KHZWIIFEFQBNKL-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=C(Cl)C=CC=C1Cl KHZWIIFEFQBNKL-UHFFFAOYSA-N 0.000 claims description 2
- KMXZEXUYXUMHEQ-UHFFFAOYSA-N 2-(4-acetylphenoxy)acetic acid Chemical compound CC(=O)C1=CC=C(OCC(O)=O)C=C1 KMXZEXUYXUMHEQ-UHFFFAOYSA-N 0.000 claims description 2
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 claims 1
- AHDPQRIYMMZJTF-UHFFFAOYSA-N 2-(3-methoxyphenoxy)acetic acid Chemical compound COC1=CC=CC(OCC(O)=O)=C1 AHDPQRIYMMZJTF-UHFFFAOYSA-N 0.000 claims 1
- CKROMSAARMUYAQ-UHFFFAOYSA-N 2-(4-butoxyphenoxy)acetic acid Chemical compound CCCCOC1=CC=C(OCC(O)=O)C=C1 CKROMSAARMUYAQ-UHFFFAOYSA-N 0.000 claims 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 229960000649 oxyphenbutazone Drugs 0.000 description 6
- CNDQSXOVEQXJOE-UHFFFAOYSA-N oxyphenbutazone hydrate Chemical compound O.O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 CNDQSXOVEQXJOE-UHFFFAOYSA-N 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 3
- 230000036269 ulceration Effects 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002008 hemorrhagic effect Effects 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 229960003329 sulfinpyrazone Drugs 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NSVKLONIKJVUPZ-UHFFFAOYSA-N 2-(4-ethoxyphenoxy)acetic acid Chemical class CCOC1=CC=C(OCC(O)=O)C=C1 NSVKLONIKJVUPZ-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR94138 | 1967-02-08 | ||
| FR118645A FR6735M (enrdf_load_stackoverflow) | 1967-02-08 | 1967-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670503A1 true DE1670503A1 (de) | 1970-04-23 |
Family
ID=26174666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681670503 Pending DE1670503A1 (de) | 1967-02-08 | 1968-02-06 | Pyrazolidindion-derivate |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT274803B (enrdf_load_stackoverflow) |
| BE (1) | BE709519A (enrdf_load_stackoverflow) |
| CH (1) | CH484147A (enrdf_load_stackoverflow) |
| DE (1) | DE1670503A1 (enrdf_load_stackoverflow) |
| FR (1) | FR6735M (enrdf_load_stackoverflow) |
| GB (1) | GB1164593A (enrdf_load_stackoverflow) |
| NL (1) | NL6801139A (enrdf_load_stackoverflow) |
| SE (1) | SE327992B (enrdf_load_stackoverflow) |
-
1967
- 1967-10-20 FR FR118645A patent/FR6735M/fr not_active Expired
-
1968
- 1968-01-17 BE BE709519D patent/BE709519A/xx unknown
- 1968-01-25 NL NL6801139A patent/NL6801139A/xx unknown
- 1968-01-31 GB GB4966/68A patent/GB1164593A/en not_active Expired
- 1968-02-01 AT AT97868A patent/AT274803B/de active
- 1968-02-06 SE SE153068A patent/SE327992B/xx unknown
- 1968-02-06 DE DE19681670503 patent/DE1670503A1/de active Pending
- 1968-02-06 CH CH169268A patent/CH484147A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE709519A (enrdf_load_stackoverflow) | 1968-05-30 |
| SE327992B (enrdf_load_stackoverflow) | 1970-09-07 |
| FR6735M (enrdf_load_stackoverflow) | 1969-02-24 |
| CH484147A (fr) | 1970-01-15 |
| AT274803B (de) | 1969-10-10 |
| GB1164593A (en) | 1969-09-17 |
| NL6801139A (enrdf_load_stackoverflow) | 1968-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2700091C2 (enrdf_load_stackoverflow) | ||
| DE2365896B2 (de) | Derivate des 4-(4-Diphenylmethylenpiperidino)-butan-l-ons und diese enthaltende Arzneimittel | |
| DE2527065A1 (de) | 5-propylthio-2-benzimidazolcarbaminsaeuremethylester | |
| DE2238504B2 (de) | l-Phenoxy-3-alkylaminopropan-2-ol -Derivate | |
| DE2160148C2 (de) | Arzneimittel und bestimmte Sulfoxide als solche | |
| DE1949813C3 (de) | 3-<4-Pvridyl)-4-(2-hydroxvphenyl)-5-alkyl-pyrazole | |
| DE2154245C3 (de) | 3-Hydrazino-6-(2-hydroxypropylamino)-pyridazinderivate, Verfahren zu ihrer Herstellung und sie enthaltendes pharmazeutisches Präparat | |
| DE2921660A1 (de) | 5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel | |
| DE1913154C3 (de) | 2-Amino-4-cyclohexylamine-s-triazin-derivate und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate | |
| DE2713933C2 (enrdf_load_stackoverflow) | ||
| DE1926359A1 (de) | oxylkansaeuren | |
| DE2457309A1 (de) | 2-phenylhydrazinothiazolin- beziehungsweise 2-phenylhydrazinothiazininderivate sowie ihre verwendung und verfahren zur herstellung derselben | |
| DE2923817C2 (de) | (3-Alkylamino-2-hydroxyproposy)-furan-2-carbonsäureanilide und deren physiologisch verträgliche Säureadditionssalze und Verfahren zu deren Herstellung sowie Arzneimittel mit einem Gehalt dieser Verbindungen | |
| DE1934392C3 (de) | Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung | |
| DE1670503A1 (de) | Pyrazolidindion-derivate | |
| DE2711149C3 (de) | N-Substituierte[4-Chlor-6-(23-xylidino)-2· pyrimidinyl- thio] essigsäureamide sowie Verfahren zu deren Herstellung | |
| EP0030343A1 (de) | Substituierte 2-Amino-3,4-dihydropyridinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE2513136B2 (de) | N-(I -Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate | |
| DE2000775B2 (de) | Substituierte 1,2,3,4-Tetrahydrobenzothieno [23-c] pyridin-Verbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitung, die diese Verbindungen enthält | |
| DE1926754A1 (de) | Neue cyclische Verbindungen,ihre Herstellung und Verwendung | |
| DE1695790C3 (de) | S-Phenoxythionocarbonylderivate des Vitamins B tief 1 | |
| CH641167A5 (en) | N-Cyano-N'-(2-((4-methyl-5-imidazolyl)-methylthio)ethyl)-N''-alkyny l guanidines | |
| DE2145359B2 (de) | 1-eckige klammer auf buten-(2)ylidenhydrazino eckige klammer zu phthalazinderivate | |
| DE3012190A1 (de) | Pharmazeutisches mittel auf der basis 1,3,5-substituierter biuret-verbindungen | |
| DE1543591C3 (enrdf_load_stackoverflow) |